Butyrfentanyl
Identification
- Summary
Butyrfentanyl is a methylated fentanyl analog with no clinical indications but is commonly used as a recreational drug.
- Generic Name
- Butyrfentanyl
- DrugBank Accession Number
- DB09173
- Background
Butyrfentanyl or butyrylfentanyl (not to be confused with 3-methylfentanyl) is a potent short-acting synthetic opioid analgesic drug.1 It is an analog of fentanyl with roughly 1/30 the potency.6 Butyrfentanyl was first synthesized in 1961 by Janssen Pharmaceuticals as a new opioid analgesic.6
Butyrfentanyl has no current legitimate clinical applications, but anecdotal reports indicate it may occasionally be surfacing on the grey-market as a recreational drug.6 This compound is a schedule I controlled substance in the USA because it is a positional isomer of 3-Methylfentanyl.7
The DEA in the United States has confirmed at least 40 fatalities involving butyrfentanyl before May 2016.6
- Type
- Small Molecule
- Groups
- Illicit
- Structure
- Weight
- Average: 350.506
Monoisotopic: 350.235813594 - Chemical Formula
- C23H30N2O
- Synonyms
- Butyr-fentanyl
- Butyrylfentanyl
- External IDs
- NIH-10486 FREE BASE
Pharmacology
- Indication
Butyrfentanyl was investigated as a potential opioid analgesic but is no longer used for this purpose.2 It is more often being used as a recreational drug.2
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Data for the pharmacodynamics of butyrfentanyl are not readily available.
- Mechanism of action
Butyrfentanyl is a µ opioid receptor agonist similar to fentanyl.6
Target Actions Organism AMu-type opioid receptor agonistHumans UKappa-type opioid receptor agonistHumans UDelta-type opioid receptor agonistHumans - Absorption
Data for the absorption of butyrfentanyl are not readily available.
- Volume of distribution
Data for the volume of distribution of butyrfentanyl are not readily available.
- Protein binding
Protein binding studies for butyrfentanyl have not been performed but due to its structural similarity with fentanyl it is likely highly bound to serum albumin and alpha-1-acid glycoprotein in circulation.5
- Metabolism
Butyrfentanyl can be N-dealkylated to nor-butyrfentanyl by CYP3A4 and CYP2D6, hydroxylated to (ω-1)-hydroxy-butyrfentanyl by CYP3A4, 4'-hydroxylated to 4'-hydroxy-butyrfentanyl, hydroxylated to ω-hydroxy-butyrfentanyl bye CYP2D6 or CYP3A4, or hydroxylated to β-hydroxy-butyrfentanyl by CYP3A4.1 ω-hydroxy-butyrfentanyl is further metabolized to ω-carboxy-butyrfentanyl while 4'-hydroxy-butyrfentanyl is further metabolized to 4'-hydroxy-3'-methoxy-butyrfentanyl.1 Many of these metabolites may undergo further conjugation reactions with glucuronic acid or sulfate.1
Hover over products below to view reaction partners
- Route of elimination
The route of elimination of butyrfentanyl has not been well described in the literature but most opioids are mainly eliminated in the urine.3
- Half-life
Data for the half life of butyrfentanyl are not readily available.
- Clearance
Data for the clearance of butyrfentanyl are not readily available.
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
The LD50 of butyrfentanyl is not readily available.8
Patients experiencing an overdose may present with sedation, altered mental state, and difficulty breathing.4 Symptoms of overdose may be treated with naloxone and supportive measures.4
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The metabolism of Butyrfentanyl can be increased when combined with Abatacept. Abiraterone The metabolism of Butyrfentanyl can be decreased when combined with Abiraterone. Acebutolol The metabolism of Butyrfentanyl can be decreased when combined with Acebutolol. Acetaminophen The metabolism of Butyrfentanyl can be decreased when combined with Acetaminophen. Adagrasib The metabolism of Butyrfentanyl can be decreased when combined with Adagrasib. - Food Interactions
- No interactions found.
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as fentanyls. These are compounds containing the fentanyl moiety or a derivative, which is based on a N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide skeleton.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Piperidines
- Sub Class
- Fentanyls
- Direct Parent
- Fentanyls
- Alternative Parents
- Phenethylamines / Anilides / Aralkylamines / Tertiary carboxylic acid amides / Trialkylamines / Amino acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- Amine / Amino acid or derivatives / Anilide / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative show 13 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 07V1H7R6ZN
- CAS number
- 1169-70-6
- InChI Key
- QQOMYEQLWQJRKK-UHFFFAOYSA-N
- InChI
- InChI=1S/C23H30N2O/c1-2-9-23(26)25(21-12-7-4-8-13-21)22-15-18-24(19-16-22)17-14-20-10-5-3-6-11-20/h3-8,10-13,22H,2,9,14-19H2,1H3
- IUPAC Name
- N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]butanamide
- SMILES
- CCCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1
References
- Synthesis Reference
Janssen PAJ. 1-Aralkyl-4-(N-aryl-carbonyl amino)piperidines and related compounds. US Patent No. US3164600 (January 5, 1965). 1965.
- General References
- Kanamori T, Iwata YT, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Inoue H: Metabolism of Butyrylfentanyl in Fresh Human Hepatocytes: Chemical Synthesis of Authentic Metabolite Standards for Definitive Identification. Biol Pharm Bull. 2019;42(4):623-630. doi: 10.1248/bpb.b18-00765. [Article]
- Baumann MH, Majumdar S, Le Rouzic V, Hunkele A, Uprety R, Huang XP, Xu J, Roth BL, Pan YX, Pasternak GW: Pharmacological characterization of novel synthetic opioids (NSO) found in the recreational drug marketplace. Neuropharmacology. 2018 May 15;134(Pt A):101-107. doi: 10.1016/j.neuropharm.2017.08.016. Epub 2017 Aug 12. [Article]
- Smith HS: Opioid metabolism. Mayo Clin Proc. 2009 Jul;84(7):613-24. doi: 10.1016/S0025-6196(11)60750-7. [Article]
- Cole JB, Dunbar JF, McIntire SA, Regelmann WE, Slusher TM: Butyrfentanyl overdose resulting in diffuse alveolar hemorrhage. Pediatrics. 2015 Mar;135(3):e740-3. doi: 10.1542/peds.2014-2878. [Article]
- Bista SR, Haywood A, Hardy J, Lobb M, Tapuni A, Norris R: Protein binding of fentanyl and its metabolite nor-fentanyl in human plasma, albumin and alpha-1 acid glycoprotein. Xenobiotica. 2015 Mar;45(3):207-12. doi: 10.3109/00498254.2014.971093. Epub 2014 Oct 14. [Article]
- World Health Organization: Butyrfentanyl Critical Review Report [Link]
- DEA: Temporary Placement of Butyryl Fentanyl and Beta-Hydroxythiofentanyl Into Schedule I [Link]
- Cayman Chemicals: Butyrylfentanyl MSDS [Link]
- External Links
- PubChem Compound
- 621174
- PubChem Substance
- 310265082
- ChemSpider
- 539764
- ZINC
- ZINC000032266443
- Wikipedia
- Butyrfentanyl
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0137 mg/mL ALOGPS logP 4.44 ALOGPS logP 4.26 Chemaxon logS -4.4 ALOGPS pKa (Strongest Basic) 8.77 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 23.55 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 108.08 m3·mol-1 Chemaxon Polarizability 42.03 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0ue9-1059000000-d58a827597ccc79bac6b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0f89-3359000000-f8c9d77bb420d1d7c60b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-6b499b9224097821e94b Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00mn-9046000000-e1729d9583e256cbde48 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0930000000-cc4bff1aca0aefc9489e Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00b9-0920000000-cbc559b03e08e30eecaa Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 201.1263288 predictedDarkChem Lite v0.1.0 [M-H]- 183.14177 predictedDeepCCS 1.0 (2019) [M+H]+ 202.6339288 predictedDarkChem Lite v0.1.0 [M+H]+ 185.53307 predictedDeepCCS 1.0 (2019) [M+Na]+ 201.4093288 predictedDarkChem Lite v0.1.0 [M+Na]+ 193.56914 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
- Gene Name
- OPRM1
- Uniprot ID
- P35372
- Uniprot Name
- Mu-type opioid receptor
- Molecular Weight
- 44778.855 Da
References
- Baumann MH, Majumdar S, Le Rouzic V, Hunkele A, Uprety R, Huang XP, Xu J, Roth BL, Pan YX, Pasternak GW: Pharmacological characterization of novel synthetic opioids (NSO) found in the recreational drug marketplace. Neuropharmacology. 2018 May 15;134(Pt A):101-107. doi: 10.1016/j.neuropharm.2017.08.016. Epub 2017 Aug 12. [Article]
- World Health Organization: Butyrfentanyl Critical Review Report [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- Molecular Weight
- 42644.665 Da
References
- Baumann MH, Majumdar S, Le Rouzic V, Hunkele A, Uprety R, Huang XP, Xu J, Roth BL, Pan YX, Pasternak GW: Pharmacological characterization of novel synthetic opioids (NSO) found in the recreational drug marketplace. Neuropharmacology. 2018 May 15;134(Pt A):101-107. doi: 10.1016/j.neuropharm.2017.08.016. Epub 2017 Aug 12. [Article]
- World Health Organization: Butyrfentanyl Critical Review Report [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
- Gene Name
- OPRD1
- Uniprot ID
- P41143
- Uniprot Name
- Delta-type opioid receptor
- Molecular Weight
- 40368.235 Da
References
- Baumann MH, Majumdar S, Le Rouzic V, Hunkele A, Uprety R, Huang XP, Xu J, Roth BL, Pan YX, Pasternak GW: Pharmacological characterization of novel synthetic opioids (NSO) found in the recreational drug marketplace. Neuropharmacology. 2018 May 15;134(Pt A):101-107. doi: 10.1016/j.neuropharm.2017.08.016. Epub 2017 Aug 12. [Article]
- World Health Organization: Butyrfentanyl Critical Review Report [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Kanamori T, Iwata YT, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Inoue H: Metabolism of Butyrylfentanyl in Fresh Human Hepatocytes: Chemical Synthesis of Authentic Metabolite Standards for Definitive Identification. Biol Pharm Bull. 2019;42(4):623-630. doi: 10.1248/bpb.b18-00765. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Kanamori T, Iwata YT, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Inoue H: Metabolism of Butyrylfentanyl in Fresh Human Hepatocytes: Chemical Synthesis of Authentic Metabolite Standards for Definitive Identification. Biol Pharm Bull. 2019;42(4):623-630. doi: 10.1248/bpb.b18-00765. [Article]
Drug created at October 14, 2015 20:53 / Updated at June 12, 2020 16:52